Technical Director, AI Programs

We’re looking for a Technical Director to provide senior technical leadership across a large, multi-stream agentic AI program. This is a leadership role, not a hands-on build role. You’ll lead through influence across internal, partner, and vendor teams, making sure every workstream is building the right thing, the right way, and solving the problem the client actually has.

In this role, you’ll provide delivery oversight across roughly ten concurrent workstreams and up to about a hundred people. You’ll validate that teams are on the right architectural path, connect their work back to client business outcomes, and step in early when something won’t land. You’ll act as the trusted technical voice with client leadership, working backwards from the outcomes the client is trying to achieve.

Why This Role Matters

At Robots & Pencils, we design AI systems for a human world. Our name says it all. Robots and pencils means engineering paired with creativity, because every agent we ship has to work for real people in real workflows. That balance is baked into how we operate.

Every role here contributes directly to that mission. Here, you shape how AI systems integrate into enterprise operations, how teams move at real velocity, and how products create measurable impact for clients and the people they serve. We ship production-ready AI in 30 to 45 days. That pace demands people who take ownership, lead with craft, and care deeply about what they put their name on.

What You’ll Do

Delivery & Technical Oversight

• Provide delivery oversight across all agentic AI workstreams, making sure each is on track to the outcomes committed to the client
• Validate that each team is building the right solution architecturally, reviewing designs, diagrams, and tradeoffs closely enough to catch flaws early
• Work backwards from the client’s business outcomes to test whether what’s being built will actually meet the need, and course correct well before a milestone or demo exposes a gap
• Read between the lines of status updates: surface hidden risks, dependency gaps, and unspoken blockers, and push teams to name and resolve them
• Join solutioning sessions, brainstorms, and client calls as needed to align direction, resolve ambiguity, and reset expectations
• Set and uphold standards for how agentic systems are designed, evaluated, secured, and prepared for production, including multi-agent orchestration, tool calling, RAG, evaluation, observability, and guardrails
• Stay close enough to the technology to go deep when it matters, using tools like Claude and Cursor to explore and pressure-test ideas

Collaboration & Communication

• Serve as the senior technical voice to client leadership, translating between architecture detail and business outcomes
• Lead across vendors, partner teams, and internal teams you don’t directly manage, building trust and alignment without relying on formal authority
• Hold direct conversations when a team is sandbagging or guarded, with the EQ to probe, ask hard questions, and drive to a clear answer, live and in the room, not only in async channels
• Partner with the engagement, product, and strategy leads who own scope and program management so technical direction and delivery stay in step
• Co-define the AI roadmap with client and R&P leadership, operating as a peer in strategic technical conversations

Leadership & Influence

• Act as the technical authority the whole program can rely on, owning high-stakes calls on architecture, risk, and delivery
• Mentor technical leads across streams, raising the bar for how teams build and communicate
• Define and champion the standards that shape how this program builds and operates agentic AI
• Drive the technical vision for the program as it scales, shaping how the work grows over the long term

What You’ll Bring

• 15+ years in engineering, data, or AI, with a career that began as an engineer and moved into leading large programs
• Experience overseeing large, multi-team programs, ideally as a director or senior director who came up through engineering; a principal-level product or technical architect who operated as the right hand to a VP or SVP is also a strong fit
• A history of being held accountable for business outcomes, not just technical delivery
• Technical depth kept sharp: you can go deep architecturally, diagram a system, weigh tradeoffs, and call out a weak design. You don’t need to be committing code daily
• Recent, real exposure to agentic AI, including agentic platforms or builds, multi-agent orchestration, tool calling, RAG, and evaluation
• Strong judgment in spotting when a team is solving the wrong problem or a solution won’t meet the client’s need
• Exceptional communication and EQ, including credibility with senior executives and comfort with conflict and hard conversations
• Experience working across multiple vendors, partners, or organizations to align on shared outcomes
• Experience in a regulated industry such as healthcare, life sciences, banking, insurance, or EdTech, including compliance regimes like SOC 2, ISO, or FERPA. Life sciences domain expertise is not required
• Working knowledge of AWS and the AWS GenAI offering (e.g., Amazon Bedrock) and other major cloud platforms
• Based in the US or Canada, with solid overlap with US Eastern or Central working hours

Helpful Extras and Unique Skills

• Experience in both product and services environments, with a clear line from business strategy to delivered outcomes
• A data science or ML background that lets you engage credibly with model and evaluation decisions
• Prior experience working alongside AWS teams or on AWS-partnered engagements

You’ll Do Well Here if You Are

• A doer. You see something broken and fix it. You’d rather move on clarity than wait for certainty.
• A fast learner who knows you don’t know everything. The AI landscape changes weekly. You’re senior enough to know better and curious enough to keep learning anyway.
• Direct in a way that makes the work better. You give honest feedback. You’d rather have the hard conversation than blow smoke.
• Obsessed with craft. You know genius is in the details. You ship exceptional, not perfect, and you don’t put your name on work you wouldn’t stand behind.
• Built for ownership. You honor commitments, admit mistakes fast, and back your teammates when a decision costs something. No handoffs, no finger-pointing.
• All in. You treat clients’ businesses like your own. You take the work seriously without taking yourself seriously.
• Resourceful when the budget, timeline, or team is tight. Constraints don’t slow you down. They sharpen you.
• Glad to be in the room with people who care as much as you do. Our teams average fifteen-plus years of experience. We hire people who push each other to do better work.